N-bromobutanimide → HCID 20728732, compound

HRID 722790Notes

Reaction equation

HRID 722790 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:18]([O:20][CH3:21])=[O:19])[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([O:16][CH3:17])=[O:15])[CH:9]=2)=[CH:6][CH:7]=1.C1C(=O)N([Br:29])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:29][CH2:1][C:2]1[CH:3]=[C:4]([C:18]([O:20][CH3:21])=[O:19])[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([O:16][CH3:17])=[O:15])[CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 20728723HCID 20728723, compound

Product 1

HCID 20728732HCID 20728732, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 4-methyl-[1,1′-biphenyl]-2,3′-dicarboxylic acid, dimethyl ester (2.26 g, 7.9 mmol) in CCl4 (50 mL) were added benzoyl peroxide (0.010 g, 0.04 mmol) and NBS (1.42 g, 8.0 mmol), and the mixture was refluxed for 3 days. The reaction mixture was allowed to cool to rt, filtered, and concentrated. The residue was purified by column chromatography (95:5 to 90:10 hexanes/EtOAc) to afford 4-bromomethyl-[1,1′-biphenyl]-2,3′-dicarboxylic acid, dimethyl ester (1.71 g, 60%): 1H NMR (DMSO-d6) δ 3.61(s, 3H), 3.88 (s, 3H), 4.84 (s, 2H), 7.48–7.50 (d, J=8.0 Hz, 1H), 7.59–7.60 (m, 2H), 7.72–7.75 (m, 1H), 7.85 (s, 1H), 7.90 (m, 1H), 7.97–7.99 (m, 1H).

Workup

  1. temperaturethe mixture was refluxed for 3 days
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (95:5 to 90:10 hexanes/EtOAc)

Sources & evidence

ORD record
ord-0f7368ce6a9d438faa40ad9de183b645
Source dataset
uspto-grants-2006_11
Patent number
US07138543B2

Reaction notes

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